WS641: Raise More Money Being An Expert Podcast Guest with Trevor Oldham

We know that podcasts are a great networking opportunity, and for syndicators, they are an excellent way to raise capital for their deals. Today’s guest, Trevor Oldham, founded Podcasting You, where he helps busy professionals get on the right podcasts. In this episode, Trevor shares how you would approach being a podcast guest.

Watch the episode here:

Listen to the podcast here:

While it’s tempting to want to go straight for the biggest podcasts out there, it’s best to start small both to get some practice and to build up credibility. We discuss the importance of getting in front of the right audience. If you are talking to everyone, you are talking to no-one, which is why you need to find the people who will resonate with what you are offering. As Trevor highlights, there is no point going on a show about mobile home parks if you are in the multifamily syndication space. Trevor walks us through how to craft our stories to ensure we are adding value to a podcasts’ audience. If you manage to get on a show where you connect with the audience, it can pay great rewards as illustrated by Trevor’s clients’ success stories. We also discuss why you should have a website prepared before going on podcasts, some interesting lead magnet ideas, and mistakes to avoid when making your podcast appearance. Be sure to tune in today!

Key Points From This Episode:

  • Trevor’s background, what led to him founding Podcasting You, and what they do.
  • What podcast guests should do if they have not been interviewed before.
  • Think about how you will benefit the hosts’ audience when appearing on a podcast.
  • Some important considerations to factor in when crafting your story.
  • Trevor’s suggestion for how long guests should talk about their background.
  • The importance of molding your story to resonate with a particular podcasts’ audience.
  • How Trevor has seen real estate syndicators benefit from being podcast guests.
  • Hear how real estate investors can add value to non-real estate podcasts.
  • Common mistakes Trevor sees guests make when they’re trying to raise money.
  • Prepare a website and lead magnets before you make any appearances on podcasts.
  • The services that Podcasting You provides and how they help their clients save time.
  • Other key things to keep in mind for investors who are trying to get on podcasts.
  • A recent business improvement, the biggest contributor to Trevor’s success, and giving back.

[bctt tweet=”If someone has never been on single podcast before, you always want to start small. — Trevor Oldham” username=”whitney_sewell”]

Links Mentioned in Today’s Episode:

Podcasting You

Trevor Oldham

Trevor Oldham Email

Joe Rogan

‎Get Off the Dental Treadmill Podcast


Listen Notes

LiveFree Investments

Logan Freeman

About Trevor Oldham

Trevor Oldham is a 23-year-old entrepreneur and founder of Podcasting You where he works with real estate investors every day to get them booked on podcasts and raise money for their syndication fund.

Full Transcript


[0:00:00.0] ANNOUNCER Welcome to the Real Estate Syndication Show. Whether you are a seasoned investor or building a new real estate business, this is the show for you. Whitney Sewell talks to top experts in the business. Our goal is to help you master real estate syndication.

And now your host, Whitney Sewell.


[0:00:24.4] WS: This is y our daily real estate syndication show. I’m your host Whitney Sewell. Today, our guest is Trevor Oldham. Thanks for being on the show, Trevor.

[0:00:33.4] TO: Thanks, Whitney. Excited to be here.

[0:00:35.7] WS: Trevor is a 23-year-old entrepreneur and founder of Podcasting You. He’s seen clients have great success raising money through being a podcast guest. He’s going to help us today and understand what that means and why it could be very important for you if you’re in the syndication business.

Trevor, thank you again for your time, appreciate you being on the show. Give us a little more of your background and maybe what Podcasting You is and let’s jump in and help the listeners a little bit.

[0:01:04.7] TO: Yeah, most certainly. I actually got started in the podcasting world back in 2015 and back then, I was actually hosting my own show. I no longer do. But within that own show, I was booking guests to be on the show and I was also getting myself booked on other podcasts just to broaden the experience of the show. Long story short, I was running that company with a partner and the partnership ultimately didn’t end up working out so I left the podcast behind.

But I made those contacts and I realized, you know, I learned a lot from getting myself booked on shows, booking guests on the show. And I was like, “Hey, maybe this is something that some people would be interested in.” I reached out to the guests that I had back on my show and I was like, “Hey, you know, I know how to get – be able to get you booked on podcasts. Is this something that you’d be interested in?” And you know, lo and behold a couple of them said yes and pretty much since 2017 on, I just started working with different people and started to just really finding the different niche industries, worked with a ton of different industries and we’ve just really found that when it comes to real estate investors, we found that they have the greatest success when they get booked on podcasts.

That essentially what our company does is we work with individuals and get them booked on podcasts to find their target audience as well.

[0:02:15.7] WS: Nice. You need to know who your target audience is, right?

[0:02:19.6] TO: Most certainly. We say, some people come on and they’re like, “I want to be on the biggest, best podcast that’s out there,” and sometimes it’s like, it’s sometimes not a fit. If you’re a self-storage investor and you’re going on a show that’s primarily for flippers, people aren’t – the message is just not going to resonate.

You really just – if you’re going to be on these podcasts, you want to make sure you’re speaking to your target audience and not – You can tell right away you can check out the podcast description, you can see the previous guest’s website. There’s tons of tools and resources out there that you can use to make sure that you’re hitting your target audience on the podcast.

[0:02:52.0] WS: You know, made me think of something else. If someone hasn’t been interviewed, maybe ever, but they know they need to get out there, and we’ll go into maybe some more detail about their story and things like that but you know, you just mentioned like the bigger podcasts or maybe with more following, side of things like that but you know, would you suggest starting there or maybe getting a little practice on a few other shows first?

[0:03:14.6] TO: I definitely recommend getting practice on a few other shows, you’ll notice that just from the beginning of when you do your first podcast to doing say your 10th podcast. Your story’s going to change and you’re going to hash out, there might be some awkward moments that come up in your first couple of interviews but you’re really able to hash it out on those smaller shows, plus you think about the show says, say it came out a month ago and you’re able to get yourself booked on a pretty relatively easy, because probably don’t have that many people wanting to be on the show.

You help out the post by being a guest on their show or they didn’t have to find you and then they help out you by helping you craft your story. I always recommend, if someone has never been on single podcast before, you always want to start small. Trust me, you don’t want to go on some of the top-tier shows that are out there and sound pretty stupid or have no idea what you’re talking about where it’s nice having those smaller shows and there’s – I don’t want to say millions but there’s a lot of different lot of real estate investing podcasts out there that are just starting every day that you can get yourself booked on.

[0:04:07.7] WS: You know, I was asked to be on a couple of bigger name shows and at that time, I hadn’t been interviewed, maybe once or twice and I postponed it until I’d been interviewed a few other times before I – you know, because I wanted to kind of perfect my story a little bit. Just like you’re talking about. Speaking of which, you know, I’d love for you to highlight on that a little bit about or talk through helping somebody think about their story and how they’re perceived by the audience and how they talk about themselves with their business and help us to think through that a little bit.

Maybe we’re not starting from complete scratch.

[0:04:43.3] TO: You know, when someone’s going on podcast, you got to think that I always think, how are you going to benefit the host’s audience? If you’re just going on spending anywhere from say 20 minutes on a shorter podcast to say an hour on longer podcast, usually, it’s not going to be three hours like a Joe Rogan Show, it’s very untypical.

You’re going to be spending this time, you want to benefit audience. When I say that you’re going out there and pitching a host instead of using words like ‘I, me or my’, you use the words like ‘you and your’. Instead of saying like, “This is how I can benefit your audience,” you can say, “This is how your audience would learn from my,” – whatever you may have, whatever your benefit may be to the audience.

When you’re crafting your story, you always want to be talking about the benefits you’re going to provide their audience. You know, let’s say you own 10 million units, whatever the number may be, that’s great but how is that going to benefit their audience, you know? You can beef yourself up as good as you want but at the end of the day, if the host is like all right, he sounds good but is he just going to come on here and pitch my services or is he going to actually provide value to my audience?

You want to make sure that you’re doing your research on the show and really targeting that show based on the benefit that  you can provide to their audience because if you can give I guess your best secrets away, people are going to be attracted to you, they’re going to go to your site and find out and learn more about you.

Just give as much value as you can to the host audience like takes a lot of work to have guest on the show and not even including the backend work. I’m sure, Whitney, you know, editing the show and getting it ready for social media and all that good stuff.

You really just want to hone in on how you’re going to be benefiting their audience and when you’re thinking about your benefits, it’s almost like what’s the number one thing that someone can learn from you? I guarantee you, t here’s someone in that audience that can learn something from you, even if it’s one person, that’s one person you touched if it’s 10, 20. However it may be.

Your story and what you’re able to share is going to be able to impact as many people as possible but even if it’s just one person, you know, I think that’s a good thing to happen.

[0:06:38.6] WS: You know, so many podcasts begin with, tell us about yourself, right? Or tell us how you got into this industry or whatever the focus is of that show, right? You know, how much time do you suggest someone spends on talking about their background or history, their company, all these things, you know, building up to maybe where they’re at now or even their – you know them personally as opposed to just their business?

[0:07:03.4] TO: I’d say about anywhere from three to five minutes, I find that sometimes best like, depending on the podcast, for myself, I’m going on like an entrepreneurial podcast, I’ll go like a way more in-depth story on how I became an entrepreneur. But I find that people like stories. “I started at zero units, I got to 500 units, this is what happened in the middle, this is a failure I encountered, these are the successes I encountered, this is how –” basically, how you got from point A to point B and then you’re able to elaborate through the rest of the interview.

I find that story of almost like a rags to riches sort of story where everyone basically starts off as a beginner. How can you help someone who is a beginner and get to where you are at that point in your life?

[0:07:43.6] WS: Ultimately, you can’t have the same story for every podcast you’re being interviewed on is that correct?

[0:07:49.8] TO: That’s correct, you definitely, if I’m speaking to your audience, you know, it’s going to be different that I’m speaking to an audience on entrepreneurship, you know, just two different audiences. I find that you know, you can really just tell the audiences that you’re speaking to just by reading the show description and checking what’s out there and you’ll notice, you know, again, you can start on the smaller shows and hone your different topics, different speeches,  what you’re going to be talking about on those smaller shows before you go on those sort of bigger shows that are out there.

[0:08:14.9] WS: Yeah, I noticed just in some of the stuff that you sent over or your team did about you being on the show that it was very – it was specific to our audience, you know, I wondered about that. It’s a great tip. Anyway, I just feel like most people, they wouldn’t be interviewed a bunch but they feel like their story’s the same can be the same every time for every show.

But let’s talk a little bit about specifically how you’re helping people even raise money specifically, you know, by being on shows and let’s talk about that specifically?

[0:08:45.5] TO: Most certainly. We had or what we’ve experienced a lot of our clients come to us that are trying to raise money for whatever deals that they may be putting together; they’re looking for investors to come in and invest in that deal. And we recently had one investor who had been with us for about a year and he just happened to mention to us that doing podcast interviews, basically he’d be going on real estate investing related shows, talking about the deals that he has going. He was able to raise millions of dollars in equity from going on to these shows.

We found that not just him but other real estate investors, where you’re able to go on to podcast and share your story and then share the deals that you have coming up and piques people’s interest into investing with you, especially if you have a nice website out there, say a lead magnet where people can learn more information about what you have to offer, it’s sort of like an easier strategy.

And plus, instead of a direct mail campaign where you send it out, you know, once, and may have to send it out a couple of more times with the podcast interview, these real estate investors are able to go on, spend however many minutes, it’s like 30 minutes or so and in that content, it’s pretty much ever green as the podcast keeps going.

Even if the deal changes which I’m assuming if someone listens to your interview a year later, they’ll probably going to know that the ideal’s not available anymore. They’ll still be able to go out and check you out. So, we’re really just see a powerful – come from people from these real estate investors going on to these podcasts and talking about themselves and talking about their deals. We found that it’s really just honing in on your target audience.

You know that the people are listening to real estate investing podcasts, one, they have an interest in real estate and usually if someone’s investing in real estate, they usually have a good amount of working capital or trying to get like a working capital. We just finally targeting this sort of high net worth investors on these shows and it’s not even just real estate investing, shows you can dentist shows, you can target doctor shows, especially when it comes to syndication and trying to raise money, you’re going after these high net worth investors, so it’s more than just real estate shows.

But we really just seen – Basically, just full access to these individuals who have the high net worth and who have that money to be able to invest with yourself or your company.

[0:10:47.1] WS: You hit a good point there too about thinking about shows that are – if you’re raising money for real estate then thinking about shows outside of just real estate, right? I love how you said you know, dentist shows, but tell me a little bit – elaborate on that a little bit but then tell me about trying to get on a show like that.

Obviously, I’m not a dentist and know nothing about it but you know, how do I get myself on that show, what’s my value, I mean, obviously, it’s about investing in real estate but you know, how do you position that that you’re going to bring value to their listeners?

[0:11:18.6] TO: What we do is we go make sure that you know, dental show, you look at them, some shows for dentist, they’re only about how to grow your dental practice, that’s honestly, that’s not going to be a fit, that’s not something we’d want to pitch a client on, it’s just dentist to dentist. You’ll find that within the dentist podcast niche, there’s shows where you know, how to build financial freedom as a dentist.

Okay, that’s a good fit; these are dentists who want to build financial freedom. What we’ll do is we’ll go out there and say, “This is one way in which your audience, your dentist can build financial freedom through real estate investing.” We really hone it into those real estate investors audience but working on the show, you ever had other people on the real estate, it’s basically come on to your show, this isn’t myself. It’s really just looking at that show description, looking at the past guests and really just making sure that it’s a dental show, usually dentist who try to raise money.

I know there’s one I believe it’s called Get Off the Dental Treadmill, you can check that show out, that’s one where that’s an example of dentists who are you know, basically stuck in the rat race working all the time, looking for financial freedom, that would be like an example of where we want to pitch clients to be on that show where it’s dentists talking about how to become financially free, it sort of just fits in to what the real estate investor would be talking about.

[0:12:29.4] WS: What about some mistakes that you see often people trying or whatever they’re doing but mistakes that are being made when they’re either trying to get on other shows like you are talking about or maybe even more so how they present themselves on the show, you know when they’re trying to raise money?

[0:12:45.2] TO: I find that people – The way that they’re going probably see as people just not – I guess just not targeting the right target audience. And I say that let’s say if you are raising money to invest in multifamily properties for example and you want to go on a show that is raising money for mobile home parks, it is not going to be fit and even if that person says, “Yes, I’d like to have you on,” chances are you are not going to see a benefit out of it. So, that is probably the number one thing we see is people not targeting the right shows.

And then two, you don’t want to just – you can create a pitch, you know and within that pitch you want to make sure you put your bio, your expertise, how are you going to benefit their audience, all that good stuff. You also want to make it personalized to that show I mean and it is super easy. Just look at the show’s description, see who they had on and then personalize it too that show.

You know for – Whitney, for your show as an example, I want to target it specifically to your audience and what you are going to be talking about and every show is going to be different. Every show is going to have different keywords within their description. So, you just want to make sure when you’re targeting a specific show. You are using sort of “their language,” and that is just a big problem we see. People just targeting the wrong shows. They just want to say, “Oh I want to be on any real estate investing podcast. I don’t care.”

It’s like no. So, you just want to make sure you’re being on the right show for your target, for the target audience you want to speak to. And then when you pitch that host, just making sure you are referencing their show and gearing towards that show as well. So, it is all just comes in full circle and make sure you are targeting the right individuals and the right host that you want to be on.

[0:14:11.9] WS: Any advice towards say having your website or a lead magnet or your call to action kind of prepared before your own shows?

[0:14:22.0] TO: Definitely a website, I would say number one. I want to say a lot of times in the past we’d had worked with clients early on that never had a website and it is going to be insanely hard to get yourself booked and if you are just using your LinkedIn account, you definitely want to have a website you could use like something like Squarespace where it might be a $150 for the year and even if you could go in and create it yourself.

So, you want to have that just make sure you have something professional as a website. It is super simple; it shouldn’t be too hard to create. It is really not that much money. It is going to make you look professional.

And then when it comes to a lead magnet, it is just something where you want to be sending the podcast listeners too, whether it is a free report, whether it’s template, whether it’s guides, any of that good stuff, courses. There is so many different things that you can create as a lead magnet so this is where you could send a podcast audience to learn more about yourself or more about your company and if they can start to get into your funnel and then you could – they are in your email list and then you can start to send them new deals that come in, they get to learn a little bit more about you. You get to promote yourself to them and in that way, they become a little bit more comfortable.

And then who knows? They came on your list today, who knows come in December they say, “Hey, I have been following this guy for a while now. I think it is time I wanted to invest in them. I’ve checked out his properties. I have seen his promotional materials; he looks pretty good.” So just starting that traction of getting someone into your funnel where maybe not today they’re going to invest with you but down the road whether that’s six months or a year it might pay off down there.

[0:15:47.6] WS: So, give us maybe a picture or paint a picture of working with you and working with a company like yourself, what does that take or out of off our plate, you know how does that benefit us?

[0:15:59.5] TO: Well certainly. So basically, what we do is if you wanted to go out there and get yourself booked on podcasts, it would be a combination of you wanting to create a podcast pitch. We use a site called You could go on there, you could search for real estate investing podcasts. You could go out and find the contact information, you could reach out to the host, do the follow up and all of that sort of stuff.

So, our company just tries to make it super simple. We’ll go out, we’ll create a pitch for you, a media kit and then on the back end we just have a database of shows of real estate investing shows that we put together with contact information, with hosts we worked with. In the past, we had the built-up relationships. So basically, we just go out there and after we had your promotional materials created, we’ll pitch you to these podcasts hosts and then we would just book your interviews on your behalf.

So, our main goal is to save you time. Anyone can go out there and get themselves booked on podcasts. It is not the hardest thing in the world. There is so many out there and I am sure if you pitch enough, someone would like to have you on. Our goal is just for someone who is a busy professional that just doesn’t want to add another thing to their plate, that is when we are able to just come in and work with you where you come with us, we learn about your backstory and then pretty much from there, we go out and handle everything from there and then we’ll be able to send you one of your interviews booked.

[0:17:09.1] WS: Nice, okay. So, what else should I have asked you or what else could you highlight for people that are trying to be on shows or maybe that we didn’t discuss?

[0:17:18.4] TO: Yeah, I think I want to touch on when someone is researching shows for themselves to be on, I tool that I find that is super useful is called and if there is anyone that wants to start, you know go out there. Start to get themselves booked on shows, you can go on You can type in say, mobile home investing. It will pull up all shows relevant of mobile home investing and then you can actually search by podcast.

So, when you first do it, it will show up by episode, you can search by podcast and then you will see it says – There is an option to choose relevance or date; you can choose date. So, this will give you the most up to date podcast and then there’s like some additional filters. You want to make sure that the podcast is in English, make sure it is in the United States, you know depending on where you are and that sort of thing and then basically you can just go through.

It gives you a link right to Apple. You can click on it, check out the podcast, see if you’d be a fit and then on another say Google sheet, you can just start keeping track of the shows you want and then you can type in the host’s name along with their podcast, get their website and then see if they have a contact form in their site. So, if someone wanted to get started that would be that process of going out there and finding shows.

Trust me, if you go to iTunes and type in real estate investing podcast it is probably going to show you the top ones that are out there and those probably shows you want to be on six months down the road, but for anyone who just wants to get started today, definitely check out I believe there is a paid version, which is a $100 a month. So, if you are serious about getting booked, it is super helpful and I highly recommend it but the free versions are definitely enough. It’s free, no dollars per month. So, it is definitely helpful if you just want to get started out, get on there say five or so podcasts and just check it out and see if that is something that you’d be interested in.

[0:18:57.3] WS: Do you have anyone in mind, say that the ideal guests, you know somebody that maybe the listener or myself could listen to, to say, “Okay, you know I hear how he presented himself, how he talked about his business, how he promoted his call to action” whatever it maybe, do you have anybody in mind like that?

[0:19:15.0] TO: Well certainly. I definitely recommend Logan Freeman, so LiveFree Investments. I believe he is out of Kansas City in Missouri. So, Logan is actually like client that I was talking about earlier in the show where he is pretty much our greatest success story where he has been able to raise millions of dollars in equity. So, his website is LiveFree Investments. So, he has been our best client to dates when it comes to raising money. So, you can definitely checkout his interviews.

On his website there is a little section where he posts all of his podcast interviews. So, someone can definitely go out and check and listen to his story, listen to how he presents itself but obviously you know, if he is able to raise a million good dollars in equity, I am sure he is doing something right on these interviews. So, I would highly recommend checking him out.

[0:19:53.8] WS: I appreciate that. Logan has been on this show a couple of times. So yeah, a listener can always search for him right here but Trevor what is a way that you have recently improved your business that we could apply to ours?

[0:20:04.5] TO: I think definitely, it’s pretty more systems in place and basically what I have done is as a business there is so many different things going on every day and I just started to create these checklists like if this happens, these are such one, two and three that you are going to do. If this happens, steps one, two and three that you are going to do, even as my assistant I started to create a frequently asked questions that I noticed that questions that she just kept asking me to answer for her.

I was like, “All right, these are the common questions I am coming in.” If any of these questions come into you, this is how you are going to answer them. So basically, I have just been implementing systems just trying to save my time as much as possible, especially the longer that you are on your business you are going to see things. You just have to run things the same way over and over and over again. Why not just document it and then just outsource it or give it to a team member to save you up some time?

[0:20:50.0] WS: What’s the number one thing that’s contributed to your success?

[0:20:53.6] TO: Definitely it is perseverance. Podcasting You this is my third company that I’ve started. I started a couple other ones in college and there has just been countless times where I’ve encountered failure even with this business there’s been times where a lot of hard lessons to learn. I remember early on I took a client and I ended up getting booked on I believe 10 or so podcasts, which at that time was a thousand dollars and then he never paid me.

So I learned the hard lesson about making sure we have contracts in place and so it is just the little things like that learning how to deal with clients and just a lot of perseverance I guess those things that are going to come up every day in business that are going to be like, “Oh man, I just want to quit right now. This sucks. I want to go and just get a good job in corporate America. It would be a lot nicer. I will have my paycheck coming in you know every two weeks.”

But you know that is the one voice inside you but just know that everyone is going to have these hard days and just really just got to push through and get to that next level and just keep on grinding like the rest of us.

[0:21:47.7] WS: Trevor, how do you like to give back?

[0:21:49.3] TO: The one thing I love doing is I go to high schools around my area and I actually speak to the students on entrepreneurship. I go through different ways in which they can get started. So, I really like to present to them and say, “Hey, you know I am a young entrepreneur, you know I am 23 years old. I graduated high school five years ago.”

And I like to say you know just age doesn’t really have a factor in your success. You can go out there and you can start a business. And I just walk them through these different ideas and how I have started my other businesses, whether that is importing products in China, whether that was starting a blog and I try to just walk through and give them business ideas and allowed them to go out and start their own business.

Because I just think that is something that is not taught enough in schools and I think that is something that they can benefit from. So, it is definitely something that I like to do a couple of times a year.

And I would just go to these different schools in Massachusetts and just talk to these students whether that’s 20 or 30. I think the largest I’ve spoken to is a crowd of a 100. I mean I say even if I touch one kid and one kid is like, “Hey, maybe I could be an entrepreneur, maybe I could be a business,” and I count that day as a win for myself.

[0:22:49.7] WS: Nice, well I appreciate you giving back in that way especially to kids that are still in school and my eyes were not opened at that time to just the opportunity of being an entrepreneur. I had no idea you know that this world is out there so I appreciate you doing that. So, tell the listeners how they can get in touch with you and learn more about you?

[0:23:07.4] TO: Well certainly, so you can check us out on our website, that is going to be and not the letter U and then if anyone has any questions, whether that is about podcasting being a podcast guest or even anything about being in entrepreneurship, you know, especially if there is a young listener out there, you know feel free to reach out to me at [email protected] and I’ll be happy to answer any questions you might have.


[0:23:30.6] WS: Don’t go yet, thank you for listening to today’s episode. I would love it if you would go to iTunes right now and leave a rating and written review. I want to hear your feedback. It makes a big difference in getting the podcast out there. You can also go to the Real Estate Syndication Show on Facebook so you can connect with me and we can also receive feedback and your questions there that you want me to answer on the show.

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